EP1041145A3 - Oligonucleotides labeled with stable isotopes and a method for detecting the same - Google Patents

Oligonucleotides labeled with stable isotopes and a method for detecting the same Download PDF

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Publication number
EP1041145A3
EP1041145A3 EP00106939A EP00106939A EP1041145A3 EP 1041145 A3 EP1041145 A3 EP 1041145A3 EP 00106939 A EP00106939 A EP 00106939A EP 00106939 A EP00106939 A EP 00106939A EP 1041145 A3 EP1041145 A3 EP 1041145A3
Authority
EP
European Patent Office
Prior art keywords
detecting
same
stable isotopes
antisense
oligonucleotides labeled
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP00106939A
Other languages
German (de)
French (fr)
Other versions
EP1041145A2 (en
EP1041145B1 (en
Inventor
Gota Kawai
Akira Wada
Hiroshi Takaku
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Taiyo Nippon Sanso Corp
Original Assignee
Japan Oxygen Co Ltd
Nippon Sanso Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Japan Oxygen Co Ltd, Nippon Sanso Corp filed Critical Japan Oxygen Co Ltd
Publication of EP1041145A2 publication Critical patent/EP1041145A2/en
Publication of EP1041145A3 publication Critical patent/EP1041145A3/en
Application granted granted Critical
Publication of EP1041145B1 publication Critical patent/EP1041145B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/113—Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2310/00—Structure or type of the nucleic acid
    • C12N2310/30—Chemical structure
    • C12N2310/31—Chemical structure of the backbone
    • C12N2310/312—Phosphonates
    • C12N2310/3125—Methylphosphonates
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2310/00—Structure or type of the nucleic acid
    • C12N2310/30—Chemical structure
    • C12N2310/31—Chemical structure of the backbone
    • C12N2310/315—Phosphorothioates
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2310/00—Structure or type of the nucleic acid
    • C12N2310/30—Chemical structure
    • C12N2310/31—Chemical structure of the backbone
    • C12N2310/318—Chemical structure of the backbone where the PO2 is completely replaced, e.g. MMI or formacetal
    • C12N2310/3181—Peptide nucleic acid, PNA
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2310/00—Structure or type of the nucleic acid
    • C12N2310/30—Chemical structure
    • C12N2310/35—Nature of the modification
    • C12N2310/351—Conjugate
    • C12N2310/3517—Marker; Tag
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Microbiology (AREA)
  • Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Immunology (AREA)
  • Analytical Chemistry (AREA)
  • Plant Pathology (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)

Abstract

Antisense oligonucleotide sequences which enable the measurement of the distribution and structure of antisense oligonucleotide drugs in the body, with lapse of time, and a method of detecting these sequences are provided. The antisense chains have a natural or non-natural nucleotide or peptide nucleic acid as a structure unit in which carbon atoms and nitrogen atoms are substituted by 13C and 15N, respectively, and the antisense chains can be detected by nuclear magnet resonance spectrometry (NMR) such as 15N-1H or 13C-1H heteronuclide multiple quantum coherence spectrometry.
EP00106939A 1999-03-31 2000-03-31 Oligonucleotides labeled with stable isotopes and a method for detecting the same Expired - Lifetime EP1041145B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11094323A JP2000290291A (en) 1999-03-31 1999-03-31 Stable isotope-labeled oligonucleotide and detection of oligonucleotide
JP9432399 1999-03-31

Publications (3)

Publication Number Publication Date
EP1041145A2 EP1041145A2 (en) 2000-10-04
EP1041145A3 true EP1041145A3 (en) 2003-12-17
EP1041145B1 EP1041145B1 (en) 2006-10-18

Family

ID=14107087

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00106939A Expired - Lifetime EP1041145B1 (en) 1999-03-31 2000-03-31 Oligonucleotides labeled with stable isotopes and a method for detecting the same

Country Status (4)

Country Link
US (3) US20030073075A1 (en)
EP (1) EP1041145B1 (en)
JP (1) JP2000290291A (en)
DE (1) DE60031320T2 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100626789B1 (en) * 2002-04-12 2006-09-22 재단법인서울대학교산학협력재단 A method for discriminating organic agricultural products from conventional agricultural products using the ratio of nitrogen isotope
JPWO2006043521A1 (en) * 2004-10-19 2008-05-22 日本新薬株式会社 Optically active oligonucleic acid compound having phosphorothioate bond
GB0604647D0 (en) * 2006-03-08 2006-04-19 Shchepinov Mikhail Stabilized food supplements and their derivatives
JP5448397B2 (en) 2007-09-07 2014-03-19 キヤノン株式会社 Substrate probe, detection method of enzyme activity by multiple nuclear magnetic resonance method, and imaging method of enzyme activity
WO2009046457A2 (en) * 2007-10-05 2009-04-09 Huntington Medical Research Institutes Imaging of genetic material with magnetic resonance
EP2276774B1 (en) 2008-03-14 2016-08-17 Retrotope, Inc. Therapeutic substances that modulate genome methylation
DK2493296T3 (en) 2009-10-30 2019-04-15 Retrotope Inc REMOVAL OF OXIDATIVE STRESS STATES WITH PUFA DERIVATIVES
AU2012249921B2 (en) 2011-04-26 2017-06-08 Biojiva Llc Oxidative retinal diseases
WO2012148926A2 (en) 2011-04-26 2012-11-01 Retrotope, Inc. Neurodegenerative disorders and muscle diseases implicating pufas
CA2834342C (en) 2011-04-26 2021-08-31 Retrotope, Inc. Impaired energy processing disorders and mitochondrial deficiency
JP6145087B2 (en) 2011-04-26 2017-06-07 レトロトップ、 インコーポレイテッドＲｅｔｒｏｔｏｐｅ， Ｉｎｃ． Disorders involving PUFA oxidation
CN102980937A (en) * 2012-11-20 2013-03-20 中国食品发酵工业研究院 Method for identifying organic coriander based on stable isotope ratio
CN102967648A (en) * 2012-11-20 2013-03-13 中国食品发酵工业研究院 Method for identifying organic hot pepper based on stable isotope ratio
EP3858843A1 (en) 2015-11-23 2021-08-04 Retrotope, Inc. Site-specific isotopic labeling of 1, 4-diene systems
WO2021168311A1 (en) 2020-02-21 2021-08-26 Retrotope, Inc. Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof
US12109194B2 (en) 2021-02-05 2024-10-08 Biojiva Llc Synergistic combination therapy for treating ALS

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6153595A (en) * 1990-08-16 2000-11-28 Isis Pharmaceuticals Inc. Composition and method for treatment of CMV infections
US6020124A (en) * 1992-04-27 2000-02-01 Trustees Of Dartmouth College Detection of soluble gene sequences in biological fluids
JPH06319581A (en) * 1993-03-15 1994-11-22 Nippon Sanso Kk Rna labeled with stabilized isotope and production of ribonucleotide
JPH07115987A (en) * 1993-10-21 1995-05-09 Nippon Sanso Kk Production of rna labeled with stable isotope
JP3581877B2 (en) * 1995-05-12 2004-10-27 独立行政法人産業技術総合研究所 Functional molecular transporter

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DELONG R K ET AL: "Comparative pharmacokinetics, tissue distribution, and tumor accumulation of phosphorothioate, phosphorodithioate, and methylphosphonate oligonucleotides in nude mice", ANTISENSE AND NUCLEIC ACID DRUG DEVELOPMENT, vol. 7, no. 2, 1997, pages 71 - 77, XP009019097, ISSN: 1087-2906 *
DUNN B E ET AL: "Helicobacter pylori", CLINICAL MICROBIOLOGY REVIEWS 1997 UNITED STATES, vol. 10, no. 4, 1997, pages 720 - 741, XP002258427, ISSN: 0893-8512 *
MACALLAN ET AL: "MEASUREMENT OF CELL PROLIFERATION BY LABELING OF DNA WITH STABLE ISOTOPE-LABELED GLUCOSE: STUDIES IN VITRO, IN ANIMALS, AND IN HUMANS", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF USA, NATIONAL ACADEMY OF SCIENCE. WASHINGTON, US, no. 95, 1998, pages 708 - 713, XP002079486, ISSN: 0027-8424 *
WEAVER L T: "Stable isotope breath tests.", NUTRITION (BURBANK, LOS ANGELES COUNTY, CALIF.) UNITED STATES OCT 1998, vol. 14, no. 10, October 1998 (1998-10-01), pages 826 - 829, XP002258370, ISSN: 0899-9007 *

Also Published As

Publication number Publication date
DE60031320T2 (en) 2007-08-30
JP2000290291A (en) 2000-10-17
EP1041145A2 (en) 2000-10-04
US20030073075A1 (en) 2003-04-17
DE60031320D1 (en) 2006-11-30
US7038036B2 (en) 2006-05-02
EP1041145B1 (en) 2006-10-18
US20060051804A1 (en) 2006-03-09
US20030104433A1 (en) 2003-06-05

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